WO2015045674A1 - ビナフタレン骨格を有するエポキシ樹脂 - Google Patents

ビナフタレン骨格を有するエポキシ樹脂 Download PDF

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Publication number
WO2015045674A1
WO2015045674A1 PCT/JP2014/071616 JP2014071616W WO2015045674A1 WO 2015045674 A1 WO2015045674 A1 WO 2015045674A1 JP 2014071616 W JP2014071616 W JP 2014071616W WO 2015045674 A1 WO2015045674 A1 WO 2015045674A1
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Prior art keywords
binaphthalene
resin
diepoxy
added
hydroxyethoxy
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PCT/JP2014/071616
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English (en)
French (fr)
Japanese (ja)
Inventor
芳範 河村
克宏 藤井
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田岡化学工業株式会社
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Application filed by 田岡化学工業株式会社 filed Critical 田岡化学工業株式会社
Priority to KR1020167009380A priority Critical patent/KR102048610B1/ko
Priority to CN201480052825.6A priority patent/CN105579488B/zh
Publication of WO2015045674A1 publication Critical patent/WO2015045674A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
    • C07D301/28—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms by reaction with hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/28—Ethers with hydroxy compounds containing oxirane rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic

Definitions

  • the present invention relates to a novel epoxy resin having a binaphthalene skeleton.
  • An epoxy resin generally becomes a cured product excellent in mechanical properties, water resistance, chemical resistance, heat resistance, electrical properties and the like by being cured with various curing agents. Therefore, epoxy resins are used in a wide range of fields such as adhesives, paints, laminates, molding materials and casting materials.
  • Patent Document 1 and Patent Document 2 include the following structural formula (2):
  • a diglycidyl ether of binaphthol represented by is disclosed.
  • the softening point of the epoxy resin of the above formula (2) described in Examples 1 to 3 is 61 to 79 ° C.
  • Patent Document 2 describes the softening point in Examples.
  • the softening point of the epoxy resin of the above formula (2) is described to be 59 to 60 ° C., and even if these are handled as solids, the softening point is low, and handling properties such as blocking due to storage conditions are difficult,
  • the use application is limited, for example, dissolution work is required.
  • An object of the present invention is to provide a novel binaphthalene skeleton-containing epoxy resin that has a binaphthalene skeleton, has a low melt viscosity, and is liquid even at room temperature, and has excellent workability and fluidity.
  • a binaphthalene skeleton-containing epoxy resin having a structure represented by the following formula (1) has a low melt viscosity and is liquid even at room temperature, It has been found that it is excellent in fluidity. Furthermore, it was also found that the binaphthalene skeleton-containing epoxy resin exhibits a high refractive index and a high Abbe number.
  • the present invention includes the following.
  • the present invention it is possible to provide a novel binaphthalene skeleton-containing epoxy resin having a binaphthalene skeleton, which is liquid even at room temperature, and excellent in workability and fluidity, and a method for producing the same. Furthermore, since the binaphthalene skeleton-containing epoxy resin of the present invention exhibits a high refractive index and a high Abbe number, it is expected to be used as a novel optical system material.
  • n is 0 or an integer of 1 or more.
  • 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene used as a raw material may be used, for example, 1,1-bi-2-naphthol.
  • 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene obtained by reacting a certain amount of ethylene carbonate or ethylene oxide in the presence of an inert solvent and an alkali catalyst may be used as it is.
  • a product purified from the reaction product after completion of the reaction using a conventional purification method (extraction, crystallization, etc.) may be used.
  • the purity of 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene used as a raw material in the present invention is usually 90% by weight or more, preferably 95% by weight or more, particularly preferably 99% by weight or more. It is.
  • alkali metal hydroxide in the present invention examples include sodium hydroxide and potassium hydroxide, and the amount used is a hydroxyl group of 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene. The amount is usually 0.8 to 4.0 moles, preferably 2.0 to 3.0 moles per mole equivalent.
  • the alkali metal hydroxide may be a solid or an aqueous solution.
  • epihalohydrin used in the present invention examples include epichlorohydrin, epibromohydrin and the like, and the amount used is a hydroxyl group of 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene.
  • the amount is usually 2 to 30 mol, preferably 3 to 20 mol, per mol equivalent.
  • the value (n number) which is the repeating unit number of diepoxy binaphthalene resin represented by the said Formula (1) can be adjusted with the usage-amount of epihalohydrin.
  • 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene with epihalohydrin for example, 2,2′-bis (2-hydroxyethoxy) -1,1 '-Binaphthalene and epihalohydrin are charged into a reaction vessel, dissolved and mixed, and then an alkali metal hydroxide is added at 20 to 120 ° C, preferably 40 to 90 ° C, and then 20 to 120 ° C, preferably 40
  • the diepoxy binaphthalene resin of the present invention can be obtained by reacting at ⁇ 90 ° C. for 1 to 24 hours.
  • Alkali metal hydroxide may be added all at once, but in order to maintain a predetermined reaction temperature, it may be added continuously by a method such as dropping over a certain period of time, for example, 1 to 10 hours, or necessary.
  • the amount is preferably added in portions.
  • the aqueous solution of the alkali metal hydroxide is continuously added to the reaction system, while the reaction system is under reduced pressure or normal pressure.
  • the mixture is brought to a reflux state, and after distilling off water and unreacted epihalohydrin, the distillate is separated, water is removed to the outside of the system, and epihalohydrin is preferably returned to the reaction system.
  • a quaternary ammonium salt such as tetramethylammonium chloride, tetramethylammonium bromide, tetrabutylammonium bromide, benzyltrimethylammonium chloride, benzyltriethylammonium chloride from the viewpoint of improving the reactivity.
  • the amount used is usually 0.01 to 0.50 mol, preferably 0.8, per 1 mol of 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene. 02 to 0.20 mol.
  • quaternary ammonium salt When a quaternary ammonium salt is used, it is usually added before adding an alkali metal hydroxide to a dissolved mixture of 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene and epihalohydrin. .
  • the diepoxy binaphthalene resin represented by the above formula (1) may be used as it is, but the post-treatment steps shown in the following ⁇ 1> to ⁇ 3> are appropriately performed to obtain the desired diepoxy biphthalene resin.
  • Naphthalene resin is preferable.
  • ⁇ 2> Ring closure step In order to obtain a diepoxy binaphthalene resin having a lower hydrolyzable halogen content, the diepoxy binaphthalene resin after the reaction or diepoxy binaphthalene subjected to a post-treatment step shown in ⁇ 1> After adding an organic solvent to the resin, an alkali metal hydroxide is added, and the mixture is usually stirred at 20 to 120 ° C., whereby a diepoxy binaphthalene resin having a smaller hydrolyzable halogen content can be obtained.
  • the organic solvent used in the ring-closing step may be any organic solvent that does not react with diepoxy binaphthalene resin or alkali metal hydroxide, and examples thereof include toluene, methyl isobutyl ketone, and methyl ethyl ketone.
  • Examples of the alkali metal hydroxide used in the ring closing step include sodium hydroxide and potassium hydroxide, which may be solid or aqueous solution, but an aqueous solution is preferably used.
  • the amount of alkali metal hydroxide used is usually 0.01-2. With respect to 1 molar equivalent of the hydroxyl group of 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene used for epoxidation. 5 moles, preferably 0.20 to 1.2 moles.
  • This ring closing step is usually carried out in 0.5 to 6 hours.
  • the reaction product obtained in the ring closure step is filtered and / or washed with water and separated to remove by-products such as tar and salts. Thereafter, neutralization is performed with an acid such as phosphoric acid, sodium phosphate, oxalic acid, acetic acid or the like so that the pH becomes 8.0 to 4.0. After neutralization, water washing and liquid separation removal are repeated, and if necessary, the insoluble matter is removed by filtration. Then, the organic solvent used in the ring-closing step is distilled off under reduced pressure to remove the diepoxy vinyl of the present invention. A naphthalene resin is obtained.
  • an acid such as phosphoric acid, sodium phosphate, oxalic acid, acetic acid or the like
  • n is 0 or an integer of 1 or more.
  • the value of n (n number) which is the number of repeating units of the diepoxy binaphthalene resin represented by the following (hereinafter also referred to as the diepoxy binaphthalene resin of the present invention), is combined with the use of the diepoxy binaphthalene resin of the present invention.
  • n number which is the number of repeating units of the diepoxy binaphthalene resin represented by the following (hereinafter also referred to as the diepoxy binaphthalene resin of the present invention)
  • n number which is the number of repeating units of the diepoxy binaphthalene resin represented by the following (hereinafter also referred to as the diepoxy binaphthalene resin of the present invention)
  • the diepoxy binaphthalene resin of the present invention is usually used as the diepoxy binaphthalene of the present invention. Used as a resin.
  • at least one of the prepared triglycidyl bodies is mixed.
  • the n number of the diepoxy binaphthalene resin of the present invention is preferably 0 or an integer of 1 to 10, more preferably 0 or an integer of 1 to 2, and most preferably 0 or 1.
  • the ratio of those having an n number exceeding 3 is increased, the compatibility is deteriorated, and there may be inconveniences such as restrictions on the amount added when the composition is used.
  • the diepoxy binaphthalene resin of the present invention is liquid at room temperature despite having a binaphthalene skeleton exhibiting features such as low water absorption and low elastic modulus at high temperatures.
  • the characteristic is low.
  • the diepoxy binaphthalene resin of the present invention has an excellent handling property because the melt viscosity at 100 ° C. is 50 to 200 mPa ⁇ s and the melt viscosity at 150 ° C. is 5 to 30 mPa ⁇ s.
  • the diepoxy binaphthalene resin of the present invention has characteristics such as high heat resistance and low viscosity, so it has excellent handling properties and can be used as a thermosetting resin raw material, a curing agent, and the like.
  • the diepoxy binaphthalene resin of the present invention may be used as it is as a general epoxy resin, or may be used as a thermosetting resin raw material such as epoxy (meth) acrylate.
  • the diepoxy binaphthalene resin of the present invention usually contains a curing agent, a diluent as necessary, a curing accelerator, and, if necessary, a conventional additive (for example, a coloring material, a stabilizer, a filler, a charging agent). It is good also as an epoxy resin composition containing a prevention material, a flame retardant, etc.).
  • the epoxy resin component contained in this epoxy resin composition may be comprised only with the diepoxy binaphthalene resin of this invention, and may be used together with another epoxy resin.
  • each measured value was measured according to the following method and measurement conditions.
  • HPLC purity The area percentage value when HPLC measurement was performed under the following measurement conditions was defined as HPLC purity.
  • ⁇ Device "LC-2010AHT” manufactured by Shimadzu Corporation Column: “L-column ODS” (5 ⁇ m, 4.6 mm ⁇ ⁇ 250 mm) manufactured by the Chemical Substance Evaluation Research Organization -Column temperature: 40 ° C ⁇
  • NMR measurement 13 C-NMR was measured under the following measurement conditions.
  • the obtained diepoxy binaphthalene resin of the present invention was dissolved in N, N-dimethylformamide to prepare 10 wt%, 20 wt% and 30 wt% solutions. Number was measured. Next, an approximate curve was derived from the three measured values obtained, and values obtained by extrapolating the approximate curve to 100% by weight were used as the refractive index and Abbe number of the obtained resin.
  • Example 1 In a 200 ml glass reaction vessel equipped with a stirrer, a cooler and a thermometer, 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene (manufactured by Taoka Chemical Industry Co., Ltd.) under a nitrogen atmosphere , Trade name TBIS-BNE) 15.00 g (0.040 mol) and epichlorohydrin 74.20 g (0.800 mol) were charged, heated to 50 ° C. and dissolved, and then 1.37 g (0.006 mol) of benzyltriethylammonium chloride. ) was added.
  • 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene manufactured by Taoka Chemical Industry Co., Ltd.
  • FIG. 1 shows a 13 C-NMR (CDCl 3 ) chart of the obtained diepoxy binaphthalene resin.
  • 115.4 to 154.2 ppm is attributed to carbon of the naphthalene skeleton, 43.9, 50.6, and 69.8 ppm are glycidyl group carbon, and 71.4 and 71.7 ppm are ethoxy group carbon. Is attributed to
  • the calculated value (TOF MS ESI + ; C 30 H 30 O 6 + Na) of the diepoxy binaphthalene resin in this analysis was 509.1940, and the actually measured value was 509.1955.
  • Example 2 In a 200 ml glass reaction vessel equipped with a stirrer, a cooler and a thermometer, 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene (manufactured by Taoka Chemical Industry Co., Ltd.) under a nitrogen atmosphere , Trade name TBIS-BNE) 15.00 g (0.040 mol) and epichlorohydrin 74.20 g (0.800 mol) were charged, heated to 50 ° C. and dissolved, and then 1.37 g (0.006 mol) of benzyltriethylammonium chloride. ) was added.
  • 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene manufactured by Taoka Chemical Industry Co., Ltd.
  • the mixture was heated to 130 ° C. and concentrated at an internal pressure of 10 mmHg. Then, it cooled to 60 degreeC and added toluene and melt
  • the organic layer was washed several times with saline and water and subjected to liquid separation removal operation, and then the organic layer was filtered to remove insoluble matters, followed by concentration under reduced pressure to obtain 16.64 g of a tan viscous liquid. (Apparent yield 85.5%) was obtained.
  • the diepoxy binaphthalene resin of the present invention or the epoxy resin composition containing the diepoxy binaphthalene resin has characteristics such as low water absorption and low elastic modulus in a high temperature range because it has a binaphthalene skeleton. Since it has a low viscosity and good workability before curing, it can be used in a wide range of fields requiring heat resistance and low viscosity. Specifically, it is useful as all electrical / electronic materials such as sealing materials, laminates, insulating materials, solder resists for printed boards, resist materials such as coverlays, color filters, and coating agents. Further, since it has characteristics of high refraction and low Abbe number, it is also useful as a raw material for optical materials. In addition, it can be used in fields such as molding materials, adhesives, composite materials, paints, printing inks, photocurable resin materials, and photosensitive resin materials.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Epoxy Resins (AREA)
  • Epoxy Compounds (AREA)
PCT/JP2014/071616 2013-09-26 2014-08-19 ビナフタレン骨格を有するエポキシ樹脂 WO2015045674A1 (ja)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020167009380A KR102048610B1 (ko) 2013-09-26 2014-08-19 바이나프탈렌 골격을 가지는 에폭시 수지
CN201480052825.6A CN105579488B (zh) 2013-09-26 2014-08-19 具有联萘骨架的环氧树脂

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JP2013199079 2013-09-26
JP2013-199079 2013-09-26

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015086361A (ja) * 2013-09-26 2015-05-07 田岡化学工業株式会社 ビナフタレン骨格を有するエポキシ樹脂

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CN116063252A (zh) * 2022-12-26 2023-05-05 北京智芯微电子科技有限公司 联萘单体及其制备方法和环氧树脂及其制备方法和应用

Citations (5)

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JPH06184131A (ja) * 1992-12-17 1994-07-05 Dainippon Ink & Chem Inc エポキシ樹脂、その製法、エポキシ樹脂組成物及び半導体封止材料
JPH07268060A (ja) * 1994-03-29 1995-10-17 Toto Kasei Kk エポキシ樹脂及びその製造方法
JP2005263778A (ja) * 2004-02-18 2005-09-29 Chisso Corp 重合性ビナフタレン誘導体
JP2008031344A (ja) * 2006-07-31 2008-02-14 Dainippon Ink & Chem Inc エポキシ樹脂組成物及びその硬化物
JP2010189534A (ja) * 2009-02-18 2010-09-02 Nippon Kayaku Co Ltd 光学レンズシート用エネルギー線硬化型樹脂組成物及びその硬化物

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US7413782B2 (en) * 2004-02-18 2008-08-19 Chisso Corporation Polymerizing binaphthalene derivatives
JP5168547B2 (ja) * 2008-02-29 2013-03-21 Ｄｉｃ株式会社 エポキシ樹脂組成物、半導体封止材料及び半導体装置
JP5292930B2 (ja) 2008-06-09 2013-09-18 住友ベークライト株式会社 半導体封止用エポキシ樹脂組成物及び半導体装置
JP2011184623A (ja) * 2010-03-10 2011-09-22 Dic Corp 硬化性樹脂組成物、その硬化物、及びプラスチックレンズ
JP6083901B2 (ja) * 2013-05-24 2017-02-22 田岡化学工業株式会社 ビナフタレン化合物の製造方法
JP6083900B2 (ja) * 2013-05-24 2017-02-22 田岡化学工業株式会社 ビナフタレン化合物の製造方法
CN105579488B (zh) * 2013-09-26 2017-07-21 田冈化学工业株式会社 具有联萘骨架的环氧树脂

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06184131A (ja) * 1992-12-17 1994-07-05 Dainippon Ink & Chem Inc エポキシ樹脂、その製法、エポキシ樹脂組成物及び半導体封止材料
JPH07268060A (ja) * 1994-03-29 1995-10-17 Toto Kasei Kk エポキシ樹脂及びその製造方法
JP2005263778A (ja) * 2004-02-18 2005-09-29 Chisso Corp 重合性ビナフタレン誘導体
JP2008031344A (ja) * 2006-07-31 2008-02-14 Dainippon Ink & Chem Inc エポキシ樹脂組成物及びその硬化物
JP2010189534A (ja) * 2009-02-18 2010-09-02 Nippon Kayaku Co Ltd 光学レンズシート用エネルギー線硬化型樹脂組成物及びその硬化物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015086361A (ja) * 2013-09-26 2015-05-07 田岡化学工業株式会社 ビナフタレン骨格を有するエポキシ樹脂

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JP6095620B2 (ja) 2017-03-15
TW201512237A (zh) 2015-04-01
JP2015086361A (ja) 2015-05-07
KR20160062037A (ko) 2016-06-01
CN105579488A (zh) 2016-05-11
TWI557149B (zh) 2016-11-11
CN105579488B (zh) 2017-07-21
KR102048610B1 (ko) 2019-11-25

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